Hydrochloric Acid → HCID 18353676, 화합물

HRID 430074노트

반응식

HRID 430074 반응식
C(O[CH:4](OCC)[CH2:5][CH2:6][NH:7][C:8]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)C.Cl.CC([O-])=O.[Na+].[Cl:29][C:30]1[CH:31]=[C:32]([CH:37]2[CH2:40][CH2:39][NH:38]2)[CH:33]=[CH:34][C:35]=1[Cl:36].C([BH3-])#N.[Na+]>C1COCC1>[Cl:29][C:30]1[CH:31]=[C:32]([CH:37]2[CH2:40][CH2:39][N:38]2[CH2:4][CH2:5][CH2:6][NH:7][C:8]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:33]=[CH:34][C:35]=1[Cl:36]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 183536582-[3,3-Diethoxypropylamino]-4-methoxyquinolineHCID 18353681HCID 18353681, 화합물

생성물 1

HCID 18353676HCID 18353676, 화합물수율 80.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-[3,3-Diethoxypropylamino]-4-methoxyquinoline (0.046 g, 0.15 mmol) in THF (4 ml) was treated with 0.5M HCl (2 ml) for 10 min. The reaction mixture was evaporated to dryness and to the residue in methanol/HOAc (1 ml/0.018 ml) was added NaOAc (0.024 g, 0.3 mmol), 2-(3,4-dichlorophenyl)azetidine (0.03 g) and sodium cyanoborohydride (0.009 g, 0.15 mmol). After reaction for 40 min at 20° C., the reaction was evaporated to dryness under reduced pressure, and the residue partitioned between ethyl acetate and sat. sodium bicarbonate. The organic layer was dried, evaporated to dryness under reduced pressure and purified by chromatography on silica gel eluting with 1-3% (9:1 MeOH/NH3) in dichloromethane to give the title compound as a colourless gum (50 mg, 80%); δH (CD3OD) 1.55 (2H, m), 2.0 (1H, m), 2.25 (1H, m), 2.45-2.7 (2H, m), 2.8 (1H, m), 3.2-3.4 (4H, m), 3.9 (3H, s), 3.95 (1H, t), 6.0 (1H, s), 7.05 (1H, t), 7.15-7.5 (5H, m), 7.8 (1H, d); MS (ES+) 416/418 (47/32%, MH+), 244 (50), 201 (100).

후처리

  1. customThe reaction mixture was evaporated to dryness and to the residue in methanol/HOAc (1 ml/0.018 ml)
  2. customAfter reaction for 40 min at 20° C.
  3. customthe reaction was evaporated to dryness under reduced pressure
  4. customthe residue partitioned between ethyl acetate and sat. sodium bicarbonate
  5. customThe organic layer was dried
  6. customevaporated to dryness under reduced pressure
  7. custompurified by chromatography on silica gel eluting with 1-3% (9:1 MeOH/NH3) in dichloromethane

출처 및 근거

ORD 기록
ord-a3078d8c9b1840909e6517502c166810
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06320051B1

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